Practicing thoughtfulness and generosity

How much does it blow you away, bowl you over, knock your socks off when someone does something incredibly generous or thoughtful for you? Being on the receiving end of unexpected kindness is a feeling unlike any other, and one that I look forward to experiencing throughout my life, even if just a few times. Part of what makes this kind of thing so special is that it’s rare and unexpected, and it’s a total day changer.

I can still remember every single time I’ve felt like this, whether from a stranger or a friend or a mate. I love that—how transformative these moments are, and how they’ve inspired me for much longer than the moment may have lasted.

Conversely, I can also remember very well every time I’ve made someone else feel this way—it might be even better than being on the receiving end! The return on investment is unparalleled; I get a truly elated feeling when I’ve made someone else’s day.

To be called thoughtful or generous is a very, very positive thing in my book. It’s a quality I notice and treasure in others, and it’s something I’ve always strived to be myself. Some people claim to not be “like that,” or they claim that’s just not how their brains work, but here’s the thing: thoughtfulness requires work for most people—it requires thought, certainly, and maybe even planning. With that in mind, I think it’s something anyone can improve upon, and it’s something that will speak volumes in your life.

So, I’ve thought about tangible ways to practice being more generous and thoughtful with those around you.

Take time to reflect on personal interactions

Maybe you just had coffee or dinner with a friend, and you spent hours catching up on each other’s lives. Or maybe you had a meeting with an employee or coworker, or a phone chat with a relative. You were (hopefully) present and interested in the moment, but maybe that’s not exactly enough for you to commit what you heard to memory. For many, this memory-recall part doesn’t come as easily. A helpful tool is to reflect on the time afterward. Spend some extra “head’ time thinking about the person and what you learned in talking to them; ask yourself questions about it; draw conclusions about it. This will help you to be able to recall more later (since you’ve turned what may have been passive listening into something more active), and hopefully circle back with the person later about something important they told you. Your care will be noticed and appreciated, and you will feel much better being able to stay in-tune with those around you. I really believe that being a good, active listener is the foundation for thoughtfulness in smaller, more subtle ways.

Pay it forward by buying someone’s coffee in the drive-through

I love the idea of this simple gesture for a stranger. I especially love that the anonymity of it could possibly inspire someone to then do the same thing for someone else. You’re not going to get recognition for this, and you’re not even going to get a thank you for it, which is why it’s a great lesson in doing something thoughtful without expecting anything in return. Just give an extra five bucks or so when you’re paying, and anything extra will just be a tip for the barista. Of course, you could also do this in person while in the coffee shop, as well.

Send snail mail

Everything is a qualifying event for sending someone a handwritten card or note—there are no rules. I doubt you’ve ever received a card for any reason and thought anything other than “that was so thoughtful!” In fact, the more obscure, the more you’ll knock the socks off your recipient. New job, new house, new city, new baby, new life direction, new nothing but I just miss you/am thinking of you/want to thank you/appreciate you/am obsessed with you/hope you’re well/wanted to say hello. Yes, it takes a little time and effort, but nowhere near the immense joy or gratitude the recipient will experience as a result.

Sneak order dessert

One of the hands-down sweetest things I’ve ever witnessed is something that Jon did when we were visiting Philadelphia for a weekend away. On our last night, we ate at this incredible little restaurant (Barbuzzo; GO there) that served Mediterranean inspired small plates. We were packed like sardines into a corner of the restaurant and as we were finishing up our dessert, a woman was sat right next to us, and she was dining alone—not in a sad way, in a comfortable and easy way that instantly made me hate myself for momentarily sympathizing her solitude. She was quiet and sweet, and from out of town as well, and she was asking us what we’d had and what we loved—she said she was quite jealous of our dessert! We conversed for a bit, and she was just a lovely person. As we were paying our bill, Jon whispered something to the waitress. I nosily begged him to keep me in the loop, but he waited until we were outside to tell me that he’d bought dessert for our new diner friend. I thought it was the sweetest thing ever, and I loved that he thought to do that, and that we’d be far gone by the time the woman found out her little surprise. I loved picturing her smile upon finding out.

Make someone cookies

This one is a no-brainer. Cookies are the OG of homemade thoughtfulness. Make some and give them away—it doesn’t matter if they’re in a Ziploc bag with a Post-it note or wrapped in an adorable box—you do you, and I promise it will be appreciated and you'll feel gratified from the entire thing.

Surprise with cocktails

Last summer, I went out to dinner with my best girl friends, and we happened to be celebrating Michelle’s graduation from business school and a ‘bon voyage’ to Ellie as she was about to embark on a cross country trip for two months. Upon being shown to our table, we were all shocked (and giddy!!) to find a chilled bottle of champagne waiting for us, with a little card stating well wishes to each of them. It was so incredibly exciting to find this mystery champagne just for us, and also made our “cheers”-ing feel so much more special. Nothing like a thoughtful little bubbly surprise to set the mood for a fantastic dinner out. PS: it had been Jon...he was at it again!

Give a hostess gift or housewarming gift

I once heard the nicest thing from a friend and her husband who moved into a new house. Amidst the overwhelming work that comes along with turning a new house into your own (i.e. painting, cleaning, unpacking, at a bare minimum), their neighbor brought them over a homemade pasta dinner—but in the cutest way. There was a container of meatballs, a separate container of sauce, and a container of noodles. I couldn’t stand how cute this was, and I immediately wanted to be a homeowner with a new neighbor to do this for—but then I remembered this is something I could really do for anyone, but especially a friend moving into a new apartment or house. I’d add in some plastic plates and flatware, a bottle of wine, and a couple of solo cups, and call it done! So. Stinking. Sweet. (Also: see my DIY granola gift)

Keep a list of ideas or things people mention that they like or care about

The key to this one is listening. The best gift givers are the best because they listen. They listen for what’s said by their friends and family casually, in passing, and without thought. Then, come Birthday or holiday time, gift-giving is much more personal, and frankly, much more fun. It’s really rewarding to give someone something intentional, thoughtful, and fitting, as opposed to those that feel more “routine” and occasion-driven. To aid this, I keep a running list in my phone notes of any ideas I have.

Use technology to your advantage

If you’re notoriously bad at remembering birthdays and other important events in your friends’ lives, that’s no longer an excuse for missing them. Learn to use your calendar and alarm and alerts to your advantage! Put every event you want to remember on your calendar, but don’t just stop there. Put another event or alert a few days before to remind yourself to send a card or gift. This is such a great way to stay ahead and stay on top of things you want to acknowledge.